Leadership Insights

A large team creating an outcomes taxonomy for justice support networks

Outcomes Taxonomy for Justice Support Networks (Cross-Org Results Funders Trust)

In the demanding world of the criminal justice system, a quarterly report is due, the intake queue is exploding, and someone asks the question that always lands hard: “So… how many people did we actually help, and what changed for them?” In a justice support network, every partner has a real story. The problem is […]

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A team trying to figure out how to know if your managed service provider is doing a good job

CEO Checklist: How to judge your Managed Service Provider on stability, risk, and business value.

Are you asking yourself the following question: “How to know if your managed service provider is doing a good job?”. This article gives you a practical checklist so you can tell the difference between an managed service provider that simply keeps the lights on and one that protects the business, supports growth, and stands up

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Cybersecurity strategy for capacity building organizations (security priorities funders will respect)

At capacity building organizations focused on workforce development, your training team is onboarding another cohort. A partner sends a spreadsheet of contacts. A funder wants a progress update, and the numbers don’t reconcile. Then someone forwards a “DocuSign” email that wasn’t DocuSign at all. Capacity building organizations sit in a tricky middle. You’re not always

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A Data Security Strategy for Court Self Help Organizations

Protecting your clients’ data isn’t just a best practice; it’s a core part of your mission. For court self-help organizations, a solid data security strategy for court self help organizations is the bedrock of public trust. It’s about moving away from last-minute fixes and building a thoughtful, proactive system to guard the sensitive information you handle

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An image of a team using remote interpretation tools for legal nonprofits

Remote Interpretation Tools for Legal Nonprofits Serving Immigrants and Refugees

Much justice work now happens on digital devices like screens or phones. Your legal teams are trying to reach clients in detention, rural towns, crowded apartments, and shelters using remote legal support. Many speak languages your team does not, or cannot find in person on short notice, requiring real-time translation. Remote interpretation tools are the

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A team learning how leaders evaluate fractional CTO partner fit for growth.

How Leaders Evaluate Fractional CTO Partner Fit For Growth

You feel it every board meeting. Technology keeps getting more expensive, more complex, and more exposed to risk, yet still feels disconnected from the actual growth plan. You do not want another tool or one more vendor pitch. You want senior leadership, without a full-time executive price tag. That is why many growth-minded CEOs are

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A team asks the questions what should a board expect to see in a cyber risk report from management

Board Cyber Oversight: What Should a Board Expect To See in a Cyber Risk Report from Management?

You have a board meeting on the calendar. The deck is almost done. But there is one slide that still feels fuzzy: the cyber risk report. Your board now treats cyber exposure the same way it treats financial exposure. Investors, lenders, and regulators see cyber risk as a direct signal of how well the business

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What is your technical debt management plan? A team discusses this.

Technical Debt Management: A CEO Investment Plan Guide for 2026

Your technology stack is talking to you. It just might be speaking in outages, manual workarounds, late projects, and anxious board questions. You already feel the drag: rising IT spend, slow decisions, finger pointing between teams, and a nagging sense that you are paying “interest” on old choices every month. That interest has a name:

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